11-Deoxy-17-phenyl-13,14-dihydro-PGE2 compounds

ABSTRACT

This invention comprises 11-deoxy-17-phenyl-18,19,20-trinor-prostaglandin-type compounds which exhibit prostaglandin-type pharmacological activity, such as lowering blood pressure, inhibiting gastric secretion, regulating the reproductive cycle, and the like.

The present application is a divisional application of Ser. No. 542,372,filed Jan. 20, 1975, now issued as U.S. Pat. No. 4,029,693, on June 14,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,029,693, issued June 14, 1977.

We claim:
 1. A compound of the formula ##STR1## or a mixture comprisingthat compound and the enantiomer thereof; WHEREIN G IS 3 TO 5,INCLUSIVE;Wherein R₁ is hydrogen, alkyl of one to 12 carbon atoms,inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one ortwo alkyl of one to 3 carbon atoms, inclusive, or chloro, or apharmacologically acceptable cation; Wherein L₁ is ##STR2## or a mixtureof ##STR3## wherein R₃ and R₄ are hydrogen or methyl, being the same ordifferent; Wherein M₁ is ##STR4## wherein R₅ and R₆ are hydrogen ormethyl, with the proviso that R₅ is methyl only when R₆ is hydrogen andR₆ is methyl only when R₅ is hydrogen; Wherein R₂₁, R₂₂, R₂₃, R₂₄, andR₂₅ are hydrogen, fluoro, chloro, trifluoromethyl, alkyl of one to 4carbon atoms, inclusive, or --OR₈ wherein R₈ is alkyl of one to 3 carbonatoms, inclusive, with the proviso that at least two of R₂₁, R₂₂, R₂₃,R₂₄, and R₂₅ are hydrogen, and not more than two of R₂₁, R₂₂, R₂₃, R₂₄,and R₂₅ are chloro, fluoro, trifluoromethyl or --OR₈.
 2. A compoundaccording to claim 1, wherein M₁ is ##STR5##
 3. A compound according toclaim 2, wherein g is
 5. 4. A compound according to claim 3, whereinR₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ are hydrogen, or four of R₂₁, R₂₂, R₂₃, R₂₄,and R₂₅ are hydrogen and one of R₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ is chloro,fluoro, or trifluoromethyl.
 5. A compound according to claim 4, whereinM₁ is ##STR6##
 6. A compound according to claim 5, wherein L₁ is##STR7##
 7. A compound according to claim 6, wherein R₁ is hydrogen,alkyl of one to 4 carbon atoms, inclusive, or a pharmacologicallycation. 8.2a,2b-Dihomo-11-deoxy-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGE₂,methyl ester, a compound according to claim
 7. 9.2a,2b-Dihomo-11-deoxy-17-phenyl-18,19,20-trinor-13,14-dihydro-PGE₂,methyl ester, a compound according to claim
 7. 10.2a,2b-Dihomo-11-deoxy-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGE₂,methyl ester, a compound according to claim
 7. 11. A compound accordingto claim 2, wherein g is
 3. 12. A compound according to claim 11,wherein R₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ are hydrogen or four of R₂₁, R₂₂,R₂₃, R₂₄, and R₂₅ are hydrogen and one of R₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ ischloro, fluoro, or trifluoromethyl.
 13. A compound according to claim12, wherein R₅ is methyl.
 14. A compound according to claim 12, whereinR₆ is methyl.
 15. A compound according to claim 12, wherein R₅ and R₆are hydrogen.
 16. A compound according to claim 15, wherein R₃ is methyland R₄ is hydrogen.
 17. A compound according to claim 15, wherein R₃ andR₄ are both methyl.
 18. A compound according to claim 15, wherein R₃ andR₄ are hydrogen. 19.11-Deoxy-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGE₂, acompound according to claim
 18. 20.11-Deoxy-17-phenyl-18,19,20-trinor-13,14-dihydro-PGE₂, a compoundaccording to claim
 18. 21.11-Deoxy-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGE₂,a compound according to claim
 18. 22. A compound according to claim 1,wherein M₅ is ##STR8##